Ent-Kauranoids isolated from Isodon eriocalyx var. laxiflora and their structure activity relationship analyses. Issue 48 (2nd December 2015)

• Record Type: Journal Article
• Authors: Wang, Wei-Guang; Yang, Jin; Wu, Hai-Yan; Kong, Ling-Mei; Su, Jia; Li, Xiao-Nian; Du, Xue; Zhan, Rui; Zhou, Min; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong
• Is Part Of: Tetrahedron. Volume 71:Issue 48(2015)
• Page Start: 9161
• Page End: 9171
• Publication Date: 2015-12-02
• Subjects: ent-Kaurane -- Diterpenoids -- Isodon; OOPMUDYZBINJQR-RPAHEMRDSA-N -- IRZIZZVHQSDVHQ-UBGOSEKISA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.09.066
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: In this report, a new cytotoxic group, a 15-oxo-16α-H-17-methoxy (or ethoxy)- unit, was suggested from the structure-activity relationship analyses of 39 ent -kaurane diterpenoids, including 17 new compounds (neolaxiflorins I–Y, 1 –17 ) isolated from the leaves of Isodon eriocalyx var. laxiflora using an in vitro cytotoxicity assay against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 human cancer cell lines. This discovery is counter to the rule that the α, β-unsaturated ketone (C-15-C-16-C-17) unit is indispensable for cytotoxicity of the ent -kauranoids. Furthermore, portions of the isolates exhibited inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages. The NF-κB inhibitory activity assay suggests a potential novel cytotoxic mechanism for compounds9 and22 . Graphical abstract: